Odor inhibition for paraffin hydrocarbons

ABSTRACT

Odor formation is inhibited in paraffin hydrocarbons of boiling point range of about 100* to about 700* F by the addition of a small amount of 2,4,6-tris-(dimethyl aminomethyl)phenol.

United States Patent [191 Reusser 'et al. v

11] 3,920,415 [451 Nov. 18, 1975 ODOR INHIBITION FOR PARAFFINHYDROCARBONS [75] Inventors: Robert E. Reusser; Lawrence 0.

Meyer, both of Bartlesville, Okla.

[73] Assignee: Phillips Petroleum Company,

Bartlesville, Okla.

22 Filed: Jan. 15, 1974 21 Appl. No.: 433,836

[52] US. Cl 44/75; 252/403 [51] Int. Cl. Cl0L 1/22 [58] Field of Search252/403; 44/75 [56] References Cited UNITED STATES PATENTS 7/1956 Fareri44/75 Primary Examiner-Delbert E. Gantz Assistant Examinerl. Vaughn [57]ABSTRACT 4 Claims, No Drawings onon INmnrrioNroR PARAFFIN IHYDROYCARBONS I BACKGROUNDOF THE INVENTION This invention relates toparaffin hydrocarbons. In one of its aspects, this invention relates toodor formation in paraffin hydrocarbons. In another of its aspects thisinvention relates to inhibition of odor formation in paraffinhydrocarbons. In one of its concepts this inl vention relates to theinhibition of an odor formation in ally, an amount in the range ofbetween about 0.005

I and 0.50 weight percent is used. A more preferable amount is in therange of about 0.01 to, about 0.20 weight percent based on the weight ofthe branched ali phatic hydrocarbons being odor-stabilized. Largeramounts can be used, if desired, but we have not found the use of largeramounts necessary. In fact increased amounts could contribute to theslight fish-like odorparaffin hydrocarbons by the addition of anantioxidant common practice to add an agent effective for inhibitingodor formation to commercial mixtures of these hydrocarbons. We havediscovered that 2,4,6-tris- (dimethyl aminomethyl)phenol added in smallamounts to paraffin hydrocarbons will inhibit oxidation and consequentlythe formation of odor bodies.

It is therefore an object of this invention to provide a paraffinhydrocarbon composition stabilized against oxidation that forms odorbodies. It is also an object of this invention to provide a method forstabilizing paraffin hydrocarbons against oxidation that forms odorbodies.

Other aspects, concepts and objects of this invention present when 0.08weight percent 2,4,6-tris-(dimethyl aminomethyl)phenol is present inSoltrol* 50. *A registered trademark of Phillips Petroleum Company Sincethe odor-stabilizing 2,4,6-tris-(dimethyl aminomethyl)phenol are solublein branched aliphatic hydrocarbons in amounts in the range stated above,special means for introducing the 2,4,6-tris-(dimethylaminomethyl)phenol into the hydrocarbons are unnecessary.

are apparent from the study of the disclosure and the appended claims. 1

SUMMARY OF THE INVENTION According to the invention, oxidation and odorformation in paraffin hydrocarbons are inhibited by the addition of2,4,6,-tris-(dimethyl aminomethyl)phenol.

In one of the embodiments of this invention an odor inhibitedcomposition of matter comprising at least one paraffin hydrocarbon and2,4,6-tris-(dimethyl aminomethyl)phenol is provided.

Materials that can be inhibited against odor formation by the process ofthis invention are paraffin hydrocarbons, or branched aliphatichydrocarbons, having a boiling point range of from about 100 to about700 F.

Although individual hydrocarbons boiling within this range can beinhibited by the process of this invention,

the process of this invention will usually be applied to mixtures ofhydrocarbons boiling within the given range. Branched aliphatichydrocarbons having a boiling point within the range of about 240 toabout 345 F such as the hydrocarbon mixtures Soltrol* 50 and S01- trol*100, marketed by Phillips Petroleum Company have been found to beparticularly well adapted to this method of odor inhibition.

The 2,4,6-tris-(dimethyl aminomethyl)phenol that has been found suitableas an odor inhibiting agent for branched aliphatic hydrocarbons isavailable commercially under the name DMP-30 from Rohm and Haas ChemicalCo.

It has been found that even a trace of 2,4,6-tris- (dimethylaminomethyl)phenol is sufficient to stabilize a branched aliphatichydrocarbon composition. Usu- The cause of odor formation in branchedaliphatic hydrocarbons has been determined to be the formation ofoxidation products which develop upon storage of the hydrocarbons. TheExample below is offered to show the effectiveness of2,4,6-tris-(dimethyl aminomethyl)phenol in preventing oxidation and,therefore, odor formation in a mixture of branched aliphatichydrocarbons.

EXAMPLE I Tests were made wherein a sample (A) of Soltrol* 50 (boilingrange of 240-300 F) with 0.08 weight percent 2,4,6-tris-(dimethylaminomethyl)phenol and a sample (B) of Soltrol* 50 alone were placed inseparate bombs in an ASTM apparatus for testing oxidation stability ofgasoline (ASTM Designation: D525-55). Oxygen was introduced into thebombs until a pressure of psig was attained and then the bombs wereplaced in hot water baths at 210 F. The pressure reached 120 psig at 210F. The percent oxygen used in the 3-day period of the tests wascalculated from the pressure drop on the bomb at various time intervals.

TABLE I No. of Days of Oxygen Consumed The control (Soltrol* 50alone)(B) had a strong oxidized hydrocarbon odor (ketone-like odor)while (A) the Soltrol* 50 with 0.08 weight percent 2,4,6-tris- (dimethylaminomethyl)phenol was water clear, but

had a slight fishlike odor. *A registered trademark of PhillipsPetroleum Company EXAMPLE II A 0.05 grams of 2,4,6-tris-(dimethylaminomethyl)- phenol was added to 100 grams of Soltrol* 50 which hadbeen percolated over 16-30 mesh attapulgite clay (sold by the MilwhiteCo., Inc., Houston, Texas) (100 m1 over g attapulgite clay) to removeodor from Soltrol* 50. A part of this mixture was set aside as theinhibited sample for the test report below. Similarly Soltrol* 50 whichhad been percolated over attapulgite clay was set aside as the controlsample. Both the control and the inhibited samples were left outdoorsex- 3 posed to sunlight at atmospheric temperature from December 22 toJune 1 in Oklahoma with the temperature varying from about F. to about100F. The samples were stored in bottles with caps loosely attached forbreathing. The samples were inspected periodically for color and odor.The results are reported in Table 11 be- 4 boiling point in the range ofabout 240F to about 345F and a stabilizing amount of2,4,6-tris-(dimethyl aminomethy1)phenol.

2. A composition of matter of claim 1 wherein 2,4,6- tris-(dimethylaminomethyl)phenol is present in an amount in the range of about 0.005to about 0.50

low. weight percent based on the weight of the branched ali- *Aregistered trademark of Phillips Petroleum Company h i h d b presentTable II No. of Days 0 8 21 83 161 Control clear clear clear water waterclear clear Color Inhibited Sample clear sl. sl. water water yellowyellow clear clear Control very very very fair bad good good good Odorlnhibited Sample fishfishfishfishgood like like like like fair It can beseen from the table above that the inhibited sample after developing aslight yellow color during the early part of the test period retainedwater clearness as did the control as test period progressed. It canalso be seen from the table above that the control sample afterregistering a very good odor for the first 21 days of the test laterdeteriorated to give a bad odor after 161 days of testing. The inhibitedsample while having a fishlike odor had deteriorated after 161 days onlyto the point of being described as having a good to fair odor.

1 claim:

1. A composition of matter consisting essentially of a mixture ofbranched paraffin hydrocarbons having a carbons present.

1. A COMPOSITION OF MATTER CONSISTING ESSENTIALLY OF A MIXTURE OFBRANCHED PARAFFIN HYDROCARBONS HAVING A BOILING POINT IN THE RANGE OFABOUT 240*F TO ABOUT 345*F AND A STABILIZING AMOUNT OF2,4,6-TRIS-(DIMETHYL AMINOMETHYL)PHENOL.
 2. A composition of matter ofclaim 1 wherein 2,4,6-tris-(dimethyl aminomethyl)phenol is present in anamount in the range of about 0.005 to about 0.50 weight percent based onthe weight of the branched aliphatic hydrocarbons present.
 3. A methodfor inhibiting odor formation in a mixture consisting essentially ofbranched paraffin hydrocarbons of boiling point range of about 240*F toabout 345*F, said method comprising the addition of a stabilizing amountof 2,4,6-tris-(dimethyl aminomethyl)phenol.
 4. A method of claim 3wherein 2,4,6-tris-(dimethyl aminomethyl)phenol is present in an amountin the range of about 0.005 to about 0.50 weight percent based on theweight of the branched aliphatic hydrocarbons present.